Patent GB-785049-A (GB)
Title: Improvements in or relating to aryloxyaliphatic compounds
Inventor: HEYWOOD BASIL JASON
IPC: C07C59/68
Filed: 1955-01-10
Abstract: The invention comprises g -chlorophenoxy-g -alkylbutyric acids of the formula <FORM:0785049/IV (a)/1> and salts, amides and esters of these acids where either R is a hydrogen atom and R1 is hydrogen, chlorine or a methyl group, or R and R1 are both chlorine atoms, and R2 is an alkyl group of not more than 4 carbon atoms, preferably a methyl group.  The compounds are made by heating the corresponding g -lactone of the formula <FORM:0785049/IV (a)/2> such as g -valerolactone with an alkali metal salt, e.g. the sodium salt, of the appropriate substituted phenol and, if desired, converting the resulting alkali metal salt of the phenoxy - butyric acid derivative into the free acid.  The products may be separated into their optical isomers.  In examples the above general method is used to prepare g -4-chloro - 2 - methylphenoxy -, 2 : 4 - dichlorophenoxy-, 2 : 4 : 5-trichlorophenoxy- and 4-chlorophenoxy derivatives of g -methylbutyric acid; also, g -(4-chloro-2-methylphenoxy)-g -methylbutyric acid is esterified to give the n-butyl and b -n-butoxyethyl esters; g -(2 : 4-dichlorophenoxy)-g -methylbutyric acid is treated with thionyl chloride and the resulting acid chloride is converted to the amide and g  - methyl - g  - (2 - methyl - phenoxy) butyric acid is chlorinated with sulphuryl chloride to give g  - (4 - chloro - 2 - methylphenoxy) - g  - methylbutyric acid.ALSO:Plant growth regulating compositions comprise a g -(chlorophenoxy)-g -alkylbutyric acid of the formula: <FORM:0785049/I/1> or a salt, ester or amide thereof, wherein R is hydrogen and R1 is hydrogen, chlorine or a methyl group or both R and R1 are chlorine atoms, and R2 is an alkyl group of not more than 4 carbon atoms (see Group IV(b)) and an inert carrier or diluent. Compositions suitable for the prevention of fruit drop comprise g -(2 : 4-dichlorophenoxy)-g -methylbutyric acid or g -(2 : 4 : 5 - trichlorophenoxy) - g  - methylbutyric acid or a salt, ester or amide thereof in association with an inert liquid or solid diluent, the concentration of the active compound being at least 0,0002 per cent by weight.  Examples describe compositions for the prevention of fruit drop comprising (17) triethanolamine salts of g  - (2 : 4 - dichlorophenoxy) - g  - methyl - butyric acid and water and (18) g  - (2 : 4 - di - chlorophenoxy) - g  - methylbutyramide, talc and kaolin.ALSO:Plant growth regulating compositions comprise a g -(chlorophenoxy)-g -alkylbutyric acid of the formula <FORM:0785049/VI/1> or a salt, ester or amide thereof, wherein R is hydrogen and R1 is hydrogen, chlorine or a methyl group or both R and R1 are chlorine atoms, and R2 is an alkyl group of not more than 4 carbon atoms (see Group IV (b)) and an inert carrier or diluent. Preferred compositions include herbicides containing a concentration of at least 0.0002 per cent of g -(4-chloro-2-methylphenoxy)-g -methylbutyric acid or a salt, ester or amide thereof in association with an inert liquid or solid diluent.  The active compounds may suitably be employed in the form of aqueous solutions of the alkali metal salts of the acids, or in solid compositions containing diluents such as talc or clay or in aqueous emulsions containing ionic or non-ionic emulsifying agents.  Examples describe herbicidal compositions comprising (10) sodium g  - (2 - methyl - 4 - chlorophenoxy) - g  - methyl-butyrate, ethylene diamine tetra-acetic acid, sodium hydroxide and water; (11) a composition according to 10 employing the potassium salt of the active compound in place of the sodium salt; (12) a composition according to 11 or 12 containing sodium lauryl sulphate; (13) g  - (4 - chloro - 2 - methylphenoxy) - g  - methylbutyric acid, diethanolamine and water; (14) a composition according to 13 employing diethylamine in place of diethanolamine; (15) compositions according to 13 and 14 containing a commercial non-ionic phenol-ethylene oxide type wetting agent; and (16) a self-emulsifying concentrate containing ethyl g -(4-chloro-2-methyl-phenoxy)-g -methyl-butyrate, sodium di-nonyl sulpho-succinate, a castor-oil-polyethylene oxide condensate and mineral oil.